This study explored how digital transformation influence the well-being and adjustment of academics at higher education institutions during organisational system and process changes. Data were collected from five purposefully selected participants through semi-structured interviews and analysed using content analysis. In this chapter, a better understanding is gained of the factors affecting change; behavioural factors that impacted academics’ well-being, and academics’ adjustment experiences. Academic well-being and adjustment are greatly influenced by digital transformation, emphasising the importance of ensuring the change process is well planned, tested and implemented by a competent team of experts. The new technology should be stable and well supported, and academics readiness for the change and digital competence should be established. Amidst experiencing numerous challenges affecting academics mentally, physically, emotionally and spiritually, they have shown great resilience in adapting personal and professional coping strategies to ensure optimal psychological well-being and adjustment.